Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation
Andrey R Galeev, Maksim V Dmitriev, Alexander S Novikov, Andrey N Maslivets
TL;DR
A new method for making substituted meta-hetarylanilines using heterocycle-substituted diketones was developed, offering efficient synthesis with good yields.
Contribution
A one-pot three-component synthesis method for meta-hetarylanilines guided by heterocycle substituents is introduced.
Findings
The electron-withdrawing power of the heterocyclic substituent influences the reaction significantly.
Meta-hetarylanilines were synthesized in 21–85% isolated yields.
The method demonstrates synthetic utility for substituted meta-hetarylanilines.
Abstract
A one-pot three-component synthesis of substituted meta-hetarylanilines from heterocycle-substituted 1,3-diketones has been developed. The electron-withdrawing power of the heterocyclic substituent (which can be estimated on the basis of calculated Hammett constants) in the 1,3-diketone plays a pivotal role in the studied reaction. The series of meta-hetarylanilines prepared (21–85% isolated yield) demonstrates the synthetic utility of the developed method.
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Multicomponent Synthesis of Heterocycles · Synthesis of heterocyclic compounds